2,2'-Dimethyl[1,1'-biphenyl]-4,4'-diamine

CAS Number 84-67-3

Chemistry Building Blocks, COF Ligands, Diamines and Dianhydrides, Monomers, Non-Heterocyclic Building Blocks, Porous Organic Frameworks

MSDS

2,2'-Dimethyl[1,1'-biphenyl]-4,4'-diamine CAS 84-67-3

A rigid biphenyl diamine building block

For the synthesis of polyimides and enamines in applications of solar cells, telecommunication applications, batteries, and separation membranes

Overview
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2,2'-Dimethyl[1,1'-biphenyl]-4,4'-diamine, CAS number 84-67-3, is a biphenyl derivative with two amines and two methyl groups. 2,2'-Dimethyl[1,1'-biphenyl]-4,4'-diamine reacts with diphenylacetaldehyde catalysed by camphorsulfonic acid forming an enamine through nucleophilic substitution and dehydration reaction. The fully conjugated enamine is a p-type semiconductor used for hole transport layers (hole mobility 2.5 × 10^-2 cm²/Vs) in solar cells (efficiency 18.4%).

2,2'-Dimethyl[1,1'-biphenyl]-4,4'-diamine is also used to synthesize low dielectric constant and low dielectric loss polyimides for telecommunication application with fast transport speed and low signal loss. The low dielectric property is achieved by the branched methyl groups enlarging the intermolecular spacing, hence the effective number of dipole moments is reduced.

General Information

CAS Number	84-67-3
Chemical Formula	C₁₄H₁₆N₂
Full Name	2,2'-Dimethyl[1,1'-biphenyl]-4,4'-diamine
Molecular Weight	212.29 g/mol
Synonyms	m-Tolidine, 2,2'-Dimethylbenzidine, 4,4'-Diamino-2,2'-dimethylbiphenyl, 4-(4-Amino-2-methylphenyl)-3-methylbenzenamine
Classification / Family	Diamine building block, Solar cells, Hole transport, Polyimides, Sensors, Telecommunication

Chemical Structure

Product Details

Purity	>99%
Melting Point	T_m = 106 °C
Appearance	White to off-white powder

MSDS Documentation

2,2'-Dimethyl[1,1'-biphenyl]-4,4'-diamine MSDS Sheet

Literature and Reviews

Enamine-based hole transporting materials for vacuum-deposited perovskite solar cell, M. Steponaitis et al., Sustainable Energy Fuels, 4, 5017-5023(2020); DOI: 10.1039/D0SE00728E.
Intrinsic low-dielectric constant and low-dielectric loss aliphatic-aromatic copolyimides: The effect of chemical structure, J. Lee et al., Mater. Today Commun., 33, 104479(2022); DOI: 10.1016/j.mtcomm.2022.104479.
Orientation control of the microphase-separated nanostructures of block copolymers on polyimides substrates, H. Maeda et al., J. Photopolym. Sci. Technol., 34(5), 439-448(2021); DOI: 10.2494/photopolymer.34.439.
Polyimide-coated glass microfiber as polysulfide per-selective separator for high-performance lithium-sulphur batteries, M.-J. Kim et al., Nanomatetrials, 9, 1612(2019); DOI: 10.3390/nano9111612.
Recent advances of thin film composite membranes for pervaporation applications: A comprehensive review, T. Zhu et al., Adv. Membr., 1, 100008(2021); DOI: 10.1016/j.advmem.2021.100008.
Solution-processable colorless polyimides derived from hydrogenated pyromellitic dianhydride: strategies to reduce the coefficients of thermal expansion by maximizing the spontaneous chain orientation behavior during solution casting, M. Hasegawa et al., Polymers, 14, 1131(2022); DOI: 10.3390/polym14061131.

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